Self-regulated learning (SRL) is crucial for fostering learner autonomy and lifelong learning skills. The article focuses on observation as a trigger of student self-feedback and self-reflection towards the development of SRL. A student peer observation programme, co-designed and piloted by teachers and researchers in two Portuguese public secondary schools is introduced, including its theoretical and methodological framework, observation scheme, and supporting observation guides. A qualitative study of self-reported effects by participating students was performed with the objectives of identifying strong aspects and possible improvements to the programme but also to gain a deeper understanding of how observation and self-feedback mediate between the performance and self-reflection phases of SRL. The results reveal an increased appreciation for feedback from various sources, and of the reflection it enables, with students emphasizing seeking help from teachers and peers. Implications for designing collaborative and student-centred learning environments with observational strategies to promote SRL are included.